#------------------------------------------------------------------------------
#$Date: 2015-12-15 09:57:53 +0200 (Tue, 15 Dec 2015) $
#$Revision: 171533 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/34/7223475.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7223475
loop_
_publ_author_name
'Gotzmann, Carla'
'Braun, Friederike'
'Bartholomä, Mark D'
_publ_section_title
;
 Synthesis,64Cu-labeling and PET imaging of 1,4,7-triazacyclononane
 derived chelators with pendant azaheterocyclic arms
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA21131J
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H33 Cu1 N9, 2(B1 F4)'
_chemical_formula_sum            'C21 H33 B2 Cu F8 N9'
_chemical_formula_weight         648.72
_chemical_name_common            'Copper NOTI-Me complex tetrafluoroborate'
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-01-13 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   11.0381(2)
_cell_length_b                   11.0381(2)
_cell_length_c                   13.1020(3)
_cell_measurement_reflns_used    6072
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      24.613
_cell_measurement_theta_min      2.638
_cell_volume                     1382.47(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle fixed chi diffractometer'
_diffrn_measurement_device_type  'Bruker Apex-II Quazar'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_laue_measured_fraction_full 0.954
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12448
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.785
_diffrn_reflns_theta_min         2.130
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0890 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.8869.
The λ/2 correction factor is 0.0000.
;
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1588
_refine_ls_number_restraints     196
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1049P)²+2.8281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1713
_reflns_Friedel_coverage         0.895
_reflns_friedel_fraction_full    0.939
_reflns_friedel_fraction_max     0.986
_reflns_number_gt                1496
_reflns_number_total             1588
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra21131j2.cif
_cod_data_source_block           ik_msd_r2_0m
_cod_original_cell_volume        1382.47(6)
_cod_database_code               7223475
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4-B2 = F4-B2A
 1.325 with sigma of 0.02
 F5-B2A = F3-B2
 1.325 with sigma of 0.02
 F2-B1
 1.325 with sigma of 0.02
 F2-B1 = F1-B1
 1.325 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
 Sof(F5)=Sof(B2A)=0.33333*(1-FVAR(3))
 Sof(F3)=Sof(B2)=0.33333*FVAR(3)
 Fixed X: B2(0) B2A(0)
 Fixed Y: B2(0) B2A(0)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.3333 0.6667 0.72093(12) 0.0306(5) Uani 1 3 d S TU P A .
N3 N 0.5153(8) 0.7409(8) 0.8025(6) 0.0407(17) Uani 1 1 d . U . . .
C1 C 0.6039(9) 0.7083(9) 0.7631(7) 0.0355(18) Uani 1 1 d . U . . .
C3 C 0.5647(15) 0.7991(13) 0.8972(9) 0.055(3) Uani 1 1 d . U . . .
H3 H 0.5204 0.8324 0.9423 0.066 Uiso 1 1 calc R . . . .
N4 N 0.7124(8) 0.7471(8) 0.8270(6) 0.0425(17) Uani 1 1 d . U . . .
C5 C 0.6808(13) 0.8014(11) 0.9149(9) 0.054(2) Uani 1 1 d . U . . .
H5 H 0.7351 0.8333 0.9755 0.065 Uiso 1 1 calc R . . . .
C7 C 0.8347(10) 0.7331(12) 0.8109(9) 0.057(3) Uani 1 1 d . U . . .
H7A H 0.8094 0.6351 0.8201 0.085 Uiso 1 1 calc GR . . . .
H7B H 0.9074 0.7915 0.8602 0.085 Uiso 1 1 calc GR . . . .
H7C H 0.8700 0.7631 0.7415 0.085 Uiso 1 1 calc GR . . . .
C6 C 0.5811(12) 0.6367(13) 0.6643(7) 0.047(2) Uani 1 1 d . U . . .
H6A H 0.5508 0.5367 0.6752 0.057 Uiso 1 1 calc R . . . .
H6B H 0.6690 0.6798 0.6243 0.057 Uiso 1 1 calc R . . . .
N1B N 0.4717(9) 0.6501(11) 0.6088(7) 0.0485(19) Uani 1 1 d . U . . .
C1A C 0.4079(17) 0.5611(19) 0.5256(12) 0.035(4) Uani 0.60(3) 1 d . U . A 1
H1AA H 0.4628 0.5173 0.5035 0.042 Uiso 0.60(3) 1 calc R . . A 1
H1AB H 0.3985 0.6130 0.4674 0.042 Uiso 0.60(3) 1 calc R . . A 1
C2A C 0.5466(18) 0.814(3) 0.5642(14) 0.036(4) Uani 0.60(3) 1 d . U . A 1
H2AA H 0.6012 0.8805 0.6193 0.043 Uiso 0.60(3) 1 calc R . . A 1
H2AB H 0.6118 0.8259 0.5082 0.043 Uiso 0.60(3) 1 calc R . . A 1
C1B C 0.359(4) 0.487(4) 0.569(2) 0.047(6) Uani 0.40(3) 1 d . U . A 2
H1BA H 0.3986 0.4617 0.5109 0.056 Uiso 0.40(3) 1 calc R . . A 2
H1BB H 0.3405 0.4194 0.6253 0.056 Uiso 0.40(3) 1 calc R . . A 2
C2B C 0.520(3) 0.740(4) 0.5372(19) 0.036(5) Uani 0.40(3) 1 d . U . A 2
H2BA H 0.4635 0.6996 0.4745 0.043 Uiso 0.40(3) 1 calc R . . A 2
H2BB H 0.6175 0.7659 0.5223 0.043 Uiso 0.40(3) 1 calc R . . A 2
F3 F 0.0000 0.0000 -0.0235(12) 0.047(3) Uani 0.72(2) 3 d DS TU P B 1
F4 F 0.1358(6) 0.0628(8) 0.1089(6) 0.073(2) Uani 1 1 d D U . . .
F1 F 0.7694(13) 0.4550(13) 0.6484(11) 0.138(4) Uani 1 1 d D U . . .
B1 B 0.6667 0.3333 0.683(2) 0.067(6) Uani 1 3 d DS TU P . .
B2 B 0.0000 0.0000 0.0799(16) 0.033(4) Uani 0.72(2) 3 d DS TU P B 1
F2 F 0.6667 0.3333 0.7849(19) 0.187(12) Uani 1 3 d DS TU P . .
F5 F 0.0000 0.0000 0.220(3) 0.048(8) Uani 0.28(2) 3 d DS TU P B 2
B2A B 0.0000 0.0000 0.117(4) 0.036(7) Uani 0.28(2) 3 d DS TU P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N3 Cu1 N3 95.3(3) 2_665 3_565
N3 Cu1 N3 95.3(3) 2_665 .
N3 Cu1 N3 95.3(3) 3_565 .
N3 Cu1 N1B 110.8(3) 2_665 3_565
N3 Cu1 N1B 110.8(3) 3_565 .
N3 Cu1 N1B 78.4(3) . .
N3 Cu1 N1B 78.4(3) 3_565 3_565
N3 Cu1 N1B 78.4(3) 2_665 2_665
N3 Cu1 N1B 110.8(3) . 2_665
N3 Cu1 N1B 153.5(3) . 3_565
N3 Cu1 N1B 153.5(3) 3_565 2_665
N3 Cu1 N1B 153.5(3) 2_665 .
N1B Cu1 N1B 80.0(3) 2_665 .
N1B Cu1 N1B 80.0(3) 2_665 3_565
N1B Cu1 N1B 80.0(3) 3_565 .
C1 N3 Cu1 113.8(6) . .
C1 N3 C3 107.9(10) . .
C3 N3 Cu1 137.4(8) . .
N3 C1 N4 109.7(9) . .
N3 C1 C6 123.1(9) . .
N4 C1 C6 127.2(9) . .
N3 C3 H3 125.4 . .
C5 C3 N3 109.2(12) . .
C5 C3 H3 125.4 . .
C1 N4 C5 105.8(8) . .
C1 N4 C7 127.2(9) . .
C5 N4 C7 127.0(9) . .
C3 C5 N4 107.3(10) . .
C3 C5 H5 126.4 . .
N4 C5 H5 126.4 . .
N4 C7 H7A 109.5 . .
N4 C7 H7B 109.5 . .
N4 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C1 C6 H6A 110.1 . .
C1 C6 H6B 110.1 . .
C1 C6 N1B 107.9(8) . .
H6A C6 H6B 108.4 . .
N1B C6 H6A 110.1 . .
N1B C6 H6B 110.1 . .
C6 N1B Cu1 108.5(6) . .
C6 N1B C2A 107.1(10) . .
C6 N1B C1B 104.4(13) . .
C1A N1B Cu1 117.0(8) . .
C1A N1B C6 117.5(10) . .
C1A N1B C2A 106.9(11) . .
C2A N1B Cu1 97.6(9) . .
C1B N1B Cu1 97.0(12) . .
C2B N1B Cu1 117.7(12) . .
C2B N1B C6 113.5(13) . .
C2B N1B C1B 114.0(19) . .
N1B C1A H1AA 110.8 . .
N1B C1A H1AB 110.8 . .
N1B C1A C2A 104.7(13) . 3_565
H1AA C1A H1AB 108.9 . .
C2A C1A H1AA 110.8 3_565 .
C2A C1A H1AB 110.8 3_565 .
N1B C2A H2AA 109.5 . .
N1B C2A H2AB 109.5 . .
C1A C2A N1B 110.9(12) 2_665 .
C1A C2A H2AA 109.5 2_665 .
C1A C2A H2AB 109.5 2_665 .
H2AA C2A H2AB 108.1 . .
N1B C1B H1BA 110.0 . .
N1B C1B H1BB 110.0 . .
H1BA C1B H1BB 108.4 . .
C2B C1B N1B 108(2) 3_565 .
C2B C1B H1BA 110.0 3_565 .
C2B C1B H1BB 110.0 3_565 .
N1B C2B C1B 110(2) . 2_665
N1B C2B H2BA 109.8 . .
N1B C2B H2BB 109.8 . .
C1B C2B H2BA 109.8 2_665 .
C1B C2B H2BB 109.8 2_665 .
H2BA C2B H2BB 108.2 . .
F1 B1 F1 109.2(12) 3_665 .
F1 B1 F1 109.2(12) 3_665 2_655
F1 B1 F1 109.2(12) . 2_655
F1 B1 F2 109.8(12) . .
F1 B1 F2 109.8(12) 2_655 .
F1 B1 F2 109.8(12) 3_665 .
F4 B2 F3 106.3(9) 3 .
F4 B2 F3 106.3(9) 2 .
F4 B2 F3 106.3(9) . .
F4 B2 F4 112.5(8) 3 2
F4 B2 F4 112.5(8) 2 .
F4 B2 F4 112.5(8) 3 .
F4 B2A F4 119.3(6) 2 .
F4 B2A F4 119.3(6) 3 .
F4 B2A F4 119.3(6) 3 2
F4 B2A F5 95(2) 3 .
F4 B2A F5 95(2) 2 .
F4 B2A F5 95(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N3 2.049(8) 2_665
Cu1 N3 2.049(8) 3_565
Cu1 N3 2.049(8) .
Cu1 N1B 2.191(8) 2_665
Cu1 N1B 2.191(8) .
Cu1 N1B 2.191(8) 3_565
N3 C1 1.306(12) .
N3 C3 1.379(14) .
C1 N4 1.344(11) .
C1 C6 1.471(13) .
C3 H3 0.9500 .
C3 C5 1.290(18) .
N4 C5 1.420(15) .
N4 C7 1.449(13) .
C5 H5 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 N1B 1.480(12) .
N1B C1A 1.399(17) .
N1B C2A 1.68(2) .
N1B C1B 1.68(4) .
N1B C2B 1.27(3) .
C1A H1AA 0.9900 .
C1A H1AB 0.9900 .
C1A C2A 1.49(3) 3_565
C2A C1A 1.49(3) 2_665
C2A H2AA 0.9900 .
C2A H2AB 0.9900 .
C1B H1BA 0.9900 .
C1B H1BB 0.9900 .
C1B C2B 1.55(4) 3_565
C2B C1B 1.55(4) 2_665
C2B H2BA 0.9900 .
C2B H2BB 0.9900 .
F3 B2 1.35(2) .
F4 B2 1.354(8) .
F4 B2A 1.304(7) .
F1 B1 1.330(14) .
B1 F1 1.330(14) 3_665
B1 F1 1.330(14) 2_655
B1 F2 1.338(19) .
B2 F4 1.354(8) 3
B2 F4 1.354(8) 2
F5 B2A 1.34(3) .
B2A F4 1.304(7) 3
B2A F4 1.304(7) 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
Cu1 N3 C1 N4 -173.1(6) .
Cu1 N3 C1 C6 5.5(11) .
Cu1 N3 C3 C5 167.7(8) .
Cu1 N1B C1A C2A -27.5(18) 3_565
Cu1 N1B C2A C1A -56.4(15) 2_665
Cu1 N1B C1B C2B 53(2) 3_565
Cu1 N1B C2B C1B 21(3) 2_665
N3 C1 N4 C5 3.2(10) .
N3 C1 N4 C7 -178.3(9) .
N3 C1 C6 N1B 17.0(13) .
N3 C3 C5 N4 2.2(13) .
C1 N3 C3 C5 -0.2(13) .
C1 N4 C5 C3 -3.3(11) .
C1 C6 N1B Cu1 -28.6(10) .
C1 C6 N1B C1A -164.1(11) .
C1 C6 N1B C2A 75.8(12) .
C1 C6 N1B C1B -131.1(14) .
C1 C6 N1B C2B 104.2(17) .
C3 N3 C1 N4 -2.0(11) .
C3 N3 C1 C6 176.6(10) .
N4 C1 C6 N1B -164.6(9) .
C7 N4 C5 C3 178.3(9) .
C6 C1 N4 C5 -175.3(9) .
C6 C1 N4 C7 3.1(14) .
C6 N1B C1A C2A 104.2(15) 3_565
C6 N1B C2A C1A -168.4(13) 2_665
C6 N1B C1B C2B 164.4(19) 3_565
C6 N1B C2B C1B -107(2) 2_665
C1A N1B C2A C1A 64.8(18) 2_665
C2A N1B C1A C2A -135.5(13) 3_565
C1B N1B C2B C1B 134(2) 2_665
C2B N1B C1B C2B -71(3) 3_565
